Chlorosuccinimide → HCID 44452192, compound

HRID 869383Notes

Reaction equation

HRID 869383 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][C:3]=1[CH:4]=[O:5].C1C(=O)N([Cl:18])C(=O)C1.OS([O-])=O.[Na+]>CC#N>[Cl:18][C:6]1[C:7]([OH:10])=[CH:8][CH:9]=[C:2]([OH:1])[C:3]=1[CH:4]=[O:5]

Participants

5

Reactant 3

HCID 31398ChlorosuccinimideHCID 709492,5-DihydroxybenzaldehydeHCID 23665763Sodium Bisulfite

Product 1

HCID 44452192HCID 44452192, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2,5-dihydroxy-benzaldehyde (100 g, 0.725 mol) was dissolved in MeCN (1L). To the solution was added NCS(N-chlorosuccinimide, 106 g, 1.1 eq) in batches under N2 protection. After addition completed, the mixture was stirred at room temperature overnight. TLC monitored the reaction. After the reaction completed, NaHSO3(38%, 500 mL) was added to the mixture, then extracted with ethyl acetate (3×600 mL) The organic layer was washed with water (2×600 mL) and brine (600 mL), dried over anhydrous MgSO4, concentrated to give a crude product, which was recrystallized to give the desired product 7A (25.6 g, 20.5% yield), as a yellow solid.

Workup

  1. additionAfter addition
  2. customthe reaction
  3. extractionextracted with ethyl acetate (3×600 mL) The organic layer
  4. washwas washed with water (2×600 mL) and brine (600 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. concentrationconcentrated
  7. customto give a crude product, which
  8. customwas recrystallized

Sources & evidence

ORD record
ord-e7485efcfcd3490d8235c65cfb0e19a2
Source dataset
uspto-grants-2015_03
Patent number
US08969373B2

Reaction notes

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